Structure Database (LMSD)

Common Name
trans-9-palmitoleic acid
Systematic Name
9E-hexadecenoic acid
Synonyms
  • trans-9-hexadecenoic acid
  • C16:1n-7
  • palmitelaidic acid
LM ID
LMFA01030057
Formula
C16H30O2
Exact Mass
Calculate m/z
254.22458
Sum Composition
FA 16:1
Status
Curated
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View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty Acids and Conjugates [FA01]
Unsaturated fatty acids [FA0103]

Biological Context

Palmitelaidic acid is a trans isomer of palmitoleic acid and dietary fatty acid that has been found in dairy fat products and various partially hydrogenated oils.1,2 It decreases nitric oxide (NO) production and levels of soluble E-selectin in isolated human aortic endothelial cells (HAECs) when used at a concentration of 20 µM.1 Palmitelaidic acid (49 µM) inhibits Sendai virus-induced hemolysis of isolated human erythrocytes.3 Increased serum levels of palmitelaidic acid are associated with higher levels of LDL, but lower levels of triglycerides, fasting insulin, blood pressure, and incidence of diabetes.2

This information has been provided by Cayman Chemical

References

1. Livingstone, K.M., Givens, D.I., Jackson, K.G., et al. Comparative effect of dairy fatty acids on cell adhesion molecules, nitric oxide and relative gene expression in healthy and diabetic human aortic endothelial cells. Atherosclerosis 234(1), 65-72 (2014).
2. MacDonald, R.C., Ore, V.D., and MacDonald, R.I. Inhibition of sendai virus-induced hemolysis by long chain fatty acids. Virology 134(1), 103-117 (1984).
3. Mozaffarian, D., de Oliveira Otto, M.C., Lemaitre, R.N., et al. trans-Palmitoleic acid, other dairy fat biomarkers, and incident diabetes: The multi-ethnic study of atherosclerosis (MESA). Am. J. Clin. Nutr. 97(4), 854-861 (2013).

Reactions

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String Representations

InChiKey (Click to copy)
SECPZKHBENQXJG-BQYQJAHWSA-N
InChi (Click to copy)
InChI=1S/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h7-8H,2-6,9-15H2,1H3,(H,17,18)/b8-7+
SMILES (Click to copy)
C(/CCCCCC)=C\CCCCCCCC(=O)O

Other Databases

Wikipedia
Palmitoleic_acid
KEGG ID
C08362
HMDB ID
HMDB0012328
CHEBI ID
59265
LIPIDBANK ID
DFA0096
PubChem CID
5282745
PlantFA ID
10052
Cayman ID
9001798

Calculated Physicochemical Properties

Heavy Atoms 18
Rings 0
Aromatic Rings 0
Rotatable Bonds 13
Van der Waals Molecular Volume 297.66
Topological Polar Surface Area 37.30
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 5.33
Molar Refractivity 77.85

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Created at
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Updated at
25th Apr 2022